有機反應（Organic synthesis）

197

Limona

常見的取代、消去有機反應機制
其實我有點寫到不知道我在寫什麼了…
有錯再跟我說
（沒有全部完成）

2025.12.20 公開

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ノートテキスト

ページ1:

1. C-C bond formation:
-H 1. NAH
> R'-X
R
R
(SN2)
HH
-R'
R
H' trans
+
SN 2
2. Ether formation:
Williamson synthesis
R-X Alkyl halid
H₂
RH₂
R'ONG
(SHZ)
H₂
R
-
But:
C
GX
OR'
Hz
R
SN 2
k
可形成不对稱醚
Can do
By
Br
CONA
OH
Condensation
R-OH H3PO4 or Hosoy
R-OH HOSOSH
D
Sub 3°C 7711 SNZ
R-
'R'
(SHI or
SN 2)
H
HÖ-R
用來合成对稱醚
R-01.
SN2
R-0²R +H₂O
→ R-O-R + H30
H
3. Alkyl halides formation from R-OH =
①用HBr
H-Br
R-OH
R-By
R-ÖH
"HABY₂
R
H₂
SIT
PBr3 or PC13
R-OH
R-OH
SNAH shift
(SN 1 or SN 2)
€
By
or R- Br + H₂O
SN2
PBr3
R-Br
(SN) or
SN2)
Br
P食
H
-Br
R
Br
+
Br
SNZ
R-Br+ HO-P-Br₂

ページ2:

c.
4. Halogenation of Carbons
basic conditions
CH3
H
0
"1
CHS
Br
何
C
Br
CH3
C-
CH3
011
J
CH3
CH3
(H3
[H3
acidic conditions
40-H
"
(SN2)会把H全部換完
=
CH3
C.
[J CECCH
CHS
SN2
-Br
CH3
+
BY
-Br
CH3
Br
TET C-C-CH:
CH3
H
HOAC
CH3
004
CH3
HOA
C-
5. Epoxides as
NaCl
CH3OH
Sub
CH3
or
ㄥ
CI
CH30%
ㄥ
OAC
NaOCH
CH3OH
basic conditions
S№2
1. Na OCH CH3
OH
2. H₂SOHO
acidic conditions
Conc HB
H₂O
OH
Br
☑
H
HBr
+ Bro
SH2
(52)
只会換1个H
H-A
C
CH3
(H3
ǐ
OH
H₂Co
(SN2)
HUCH
OOH + OCH 3
: →接取代基少的
16
H-OH₂
SN 2
b. Formation of expoxides
OH
orl
NabH
Mon, 24hr
+160
(SN2)
+ C16
OH
H
-CH₂
+B0
-CH3
Br

ページ3:

7. Diazomethane Formation of Lo-
[H₂ Na
OH
E.O. CH. Cla
30min
LẶC - NÊN HỌC NÊN
CHC-
8. Quaternary Ammonium Salts
6
+
N-19)
無副產物
HBC-NEN:
`OH + N>19)
SN 2
Br
NH3
①
R-
NHz
R
NH3
R-BY
R-HAH
H₂ NH3
R-NH2 + NH4
HJ
R
②
R-
NH₂ R-Br
-
R-N
→中途不会停下
repeat
R
R-NH₂
R-Br
SH
R-N
NH3
"R-Br
=NH3
SN2
R
R-NR
RR
R
9. Hofmann
elim
NH₂
1. CHBI (excess)
3.Ag.0 3.0
N
(E₂)
选取代基中的→!多的那週沒anti H
HH₂
H-
HSC
+10
NH HN
ON
+ I& Ag₂O
JOH
repeat
Ez
HR
10. Generating Alkynes
Re-cat
R₁
H
C=C
'R'
PL
Base
R-C=C-R'
Box-CR-C = C-R'
R
• terminal alkyne
ON-
QN
H'
H
=
DMF, 0°C, 1hr
Br 2. NHAC HO
H
H
QN
Ez
NHACI Acid workup
AHRGH ON-
e
add
H+ trans 停不下來
+ NH3